(S)-2-((4S,6S)-4,6-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-4-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexanone

Base Information

• Chemical Name: (S)-2-((4S,6S)-4,6-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-4-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexanone
• CAS No.: 177570-14-8
• Molecular Formula: C₁₆H₂₇O₆P
• Molecular Weight: 346.361

Synonyms:(S)-2-((4S,6S)-4,6-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-4-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexanone

Chemical Property of (S)-2-((4S,6S)-4,6-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-4-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexanone

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Technology Process of (S)-2-((4S,6S)-4,6-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-4-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexanone

There total 3 articles about (S)-2-((4S,6S)-4,6-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-4-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(4S,6S)-4,6-Dimethyl-2-[4-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohex-1-enyloxy]-[1,3,2]dioxaphosphinane 2-oxide → (R)-2-((4S,6S)-4,6-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-4-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexanone + (S)-2-((4S,6S)-4,6-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-4-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexanone (177570-14-8)

Guidance literature:

With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium diisopropyl amide; In tetrahydrofuran; for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo9518157

Reference yield:

(2S,4S)-pentane-2,4-diol (72345-23-4) → (S)-2-((4S,6S)-4,6-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-4-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexanone (177570-14-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / POCl₃, Et₃N / benzene / 15 h / Ambient temperature

2: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C to room temperature; room temperature, 4 h

3: LDA, LTMP / tetrahydrofuran / 5 h / Ambient temperature

With 2,2,6,6-tetramethylpiperidinyl-lithium; triethylamine; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; benzene;

DOI:10.1021/jo9518157

Reference yield:

(4S,6S)-2-Chloro-4,6-dimethyl-[1,3,2]dioxaphosphinane 2-oxide (177570-11-5) → (S)-2-((4S,6S)-4,6-Dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-yl)-4-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexanone (177570-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C to room temperature; room temperature, 4 h

2: LDA, LTMP / tetrahydrofuran / 5 h / Ambient temperature

With 2,2,6,6-tetramethylpiperidinyl-lithium; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo9518157

upstream raw materials:

(2S,4S)-pentane-2,4-diol

(4S,6S)-2-Chloro-4,6-dimethyl-[1,3,2]dioxaphosphinane 2-oxide

Downstream raw materials:

(4S)-(+)-4-methyl-4-(2-methyl-1,3-dioxolan-2-yl)-2-methylenecyclohexanone

2-[(1S,3S)-3-(2,5-Dimethoxy-benzyl)-1,3-dimethyl-4-methylene-cyclohexyl]-2-methyl-[1,3]dioxolane

(2S,4S)-2-(2,5-Dimethoxy-benzyl)-2,4-dimethyl-4-(2-methyl-[1,3]dioxolan-2-yl)-cyclohexanone

1-[(1S,3S,4S)-3-(2,5-Dimethoxy-benzyl)-1,3,4-trimethyl-cyclohexyl]-ethanone

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